1,4-Dibromobenzene → HCID 86762388、化合物

HRID 1021175ノート

反応式

HRID 1021175 の反応式
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([N:7]([C:30]2[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=2)[C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 78041,4-DibromobenzeneHCID 23676156Sodium t-butoxideHCID 86762387Biphenyl-4-yl-biphenyl-2-yl-amin

生成物 1

HCID 86762388HCID 86762388、化合物収率 87%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒

実験手順

Toluene (500 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.4 g, 1.7 mmol) and Pd(OAc)2 (0.10 g, 0.42 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (6.7 g, 21.0 mmol), 1,4-dibromobenzene (14.9 g, 63.0 mmol), sodium tert-butoxide (4.0 g, 42.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 12 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene (containing 0.5% triethylamine). The solvent was removed in vacuo and the residue was purified by flash chromatography using 10-20% toluene/hexane (containing 0.5% triethylamine) to afford N-([1,1′-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1′-biphenyl]-2-amine (8.7 g, 87% yield) as a white solid.

後処理

  1. customToluene (500 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 12 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with toluene (containing 0.5% triethylamine)
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-fd0095f01a244f86af9fc3ad4e05623c
出典データセット
uspto-grants-2014_05
特許番号
US08716484B1

反応ノート

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